Q: All ethics aside, do you think you could make more money obtaining sensitive information about high net worth individuals and using blackmail/extortion to get money from them, instead of writing books, founding companies, etc.?

A: Basically, you’re asking if crime pays. Most of the time, it doesn’t, and the problem is the different risk characteristics. If I make a computer security mistake — in a book, for a consulting client, at BT — it’s a mistake. It might be expensive, but I learn from it and move on. As a criminal, a mistake likely means jail time — time I can’t spend earning my criminal living. For this reason, it’s hard to improve as a criminal. And this is why there are more criminal masterminds in the movies than in real life.